During anandamide biosynthesys 1-arachidonoyl-2-stearoyl-sn-glycerol
3-phospho ethanolamine and
1,2-diarachidonoylphosphatidylcholine pass to a
transacylation reaction catalyzed by HRAS-like suppressor 5
(HRSL5) [1] and also by Arylamine
N-acetyltransferase (NAT) that gives
N,1-diarachidonoyl-2-stearoyl-sn-glycerol
3-phosphoethanolamine and either 2-arachidonoyl-glycerol
3-phosphocholine or
1-arachidonoyl-sn-glycero-3-phosphocholine as products.

N,1-Diarachidonoyl-2-stearoyl-sn-glycerol
3-phosphoethanolamine undergoes multiple transformations. It can either be
hydrolyzed by N-acyl-phosphatidylethanolamine-hydrolyzing phospholipase D
(NAPE PLD) to form directly
Anandamide and also
1-arachidonoyl-2-stearoyl-glycerol 3-phosphate as a
byproduct [2], [3], [4]; either can be hydrolyzed
by the action of various phospholipases (Phospholipase A2
(PLA2(hGIIA)), Cytosolic phospholipase A2
(PA24A), Group 10 secretory phospholipase A2 precursor
(PLA2G10), Calcium-dependent phospholipase A2 precursor
(PLA2G5)) to form Arachidonic
acid and N-arachidonoyl-2-stearoyl-sn-glycerol
3-phosphoethanolamine [5], [6], [7]. The same metabolite is formed in when HRSL5
catalyses the intramolecular transacylation of
1-arachidonoyl-2-stearoyl-sn-glycerol 3-phospho ethanolamine
[1].

Another way is degradation under the action of Phospholipase A2 precursor
(PLA2G1B) with N,1-diarachidonoyl-sn-glycerol
3-phosphoethanolamine metabolite and Stearic
acid as a byproduct [5]. Ectonucleotide
pyrophosphatase/phosphodiesterase family member 2 precursor
(ENPP2) acts on N,1-diarachidonoyl-sn-glycerol
3-phosphoethanolamine causing its hydrolysis what leads to the production
of Anandamide and 1-arachidonoyl-glycerol
3-phosphate [5]. 1-arachidonoyl-glycerol
3-phosphate can also be formed during ENPP2
catalyzed 1-arachidonoyl-glycerol 3-phosphate hydrolysis
and 2-arachidonoyl-glycerol 3-phosphate is formed during an
analogous process with 2-arachidonoyl-glycerol
3-phosphocholine as a substrate. Both processes give
Choline as a byproduct [8], [9], [10], [11], [12].

Finally, N,1-diarachidonoyl-2-stearoyl-sn-glycerol
3-phosphoethanolamine can be hydrolyzed by a set of phospholipases
(PLC-delta, PLC-gamma,
phospholipase C, zeta 1 (PLC-zeta),
PLC-beta, 1-phosphatidylinositol-4,5-bisphosphate
phosphodiesterase epsilon-1 (PLC-epsilon)) to form
1-arachidonoyl-2-stearoyl-sn-glycerol and
phosphoanandamide [13].
Phosphoanandamide is subjected to phosphatase activity of
Tyrosine-protein phosphatase non-receptor type 22 (70Z-PEP)
and Anandamide together with a
phosphate unit are formed [13].

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